There’s nothing quite like summer in Chicago. All season long, you can play beach volleyball on the sandy shores of Lake Michigan, kayak through a skyscraper canyon, sip cocktails from rooftop bars with skyline views — the list goes on and on. Here’s your guide to making the most out of summer in Chicago.

Hit the beach

Photo by Miguel Ángel Sanz

Chicago is blessed with miles and miles of sandy lakefront beaches. Build a sandcastle empire at Foster Beach, cool off at trendy Shore Club Chicago (where you can reserve a daybed or a cabana) at North Avenue Beach, or simply enjoy the view (and catch a beach volleyball game) at Oak Street Beach. If you’re a bit of a thrill-seeker, you can rent a jet ski, kayak, paddleboard, or fly board at Chicago Water Sport Rentals at 31st Street Harbor.

Check out our guide to Chicago beaches for more.

Dine outside

Chicago is home to a wealth of outdoor dining options, whether you want to sip wine on a waterfront patio or enjoy craft cocktails on a scenic rooftop.

Or just stroll through any neighborhood in Chicago, and you’ll have plenty of stellar alfresco spots to choose from.

Take a boat cruise

Each summer, Chicago’s many boat cruises set sail on Lake Michigan and the Chicago River. There’s tons of different Chicago cruise options for a variety of interests, from leisurely dinner cruises to educational architecture tours to high-speed thrill rides.

Hop on a Chicago Architecture Foundation Center River Cruise to hear the fascinating stories behind the city’s iconic architecture and historic buildings from expert tour guides. Or get your heart pumping on a fast-paced Seadog Cruise. Island Party Hut brings the tiki vibes, while Odyssey offers a more refined dinner experience on a unique all-glass.

Odyssey Chicago River

Explore all your options with our guide to Chicago boat cruises and tours.

Jam out, outside

Festival season is back in Chicago. And it’s not really summer until you check out one of our legendary music events, ranging from neighborhood block parties with local bands to sprawling outdoor fest with major headlining acts. Here are a few music festivals to check out in Chicago this summer:

Check out our full summer music festival guide for more.

Get out on the water

Chicago is home to two stunning waterfronts — Lake Michigan, with miles of sandy shoreline, and the Chicago River, a skyscraper canyon through the heart of the city. And both offer plenty of opportunities to get out on the water. You can rent jet skis and paddleboards on the lakefront and kayaks on the river and lake. You can also rent all types of boats, from small electric vessels to pontoon party boats, on the lake and river.

See Navy Pier

Navy Pier Shoreline Boats

Historic lakefront Navy Pier is one of the city’s most popular attractions. Here’s just a sample of the many things to see and do there during the summer:

Head to a rooftop

Chicago’s skyline is filled with rooftop bars and restaurants, perfect for cocktails and bites on a sunny afternoon or warm summer’s evening. One local favorite is LH Rooftop, which wows with the city’s only tri-level rooftop lounge overlooking the Chicago River. VU Rooftop offers a rare view of the Chicago skyline from the South Loop. And Cabana Club in Wicker Park is a hip hangout with indoor-outdoor space, a tiny pool, chairs for sunbathing, and seasonal cocktails.

Find even more sky-high options with our guide to rooftop bars.

See a museum exhibit

This summer brings a slate of jaw-dropping exhibits to Chicago. Step inside a moving Van Gogh painting, explore the works of Frida Kahlo, come face-to-face with the Obamas, meet Marvel superheroes, and more at these excited limited-time exhibits:

Explore more top museum exhibits coming to Chicago this summer.

Explore a city park

The Chicago Park District oversees more than 600 parks, with open space in just about every corner of the city. Millennium Park’s free Lurie Garden is an urban oasis in the heart of the Loop. Also nearby, you can let the kids climb, skate, and play at the sprawling Maggie Daley Park. Head to our neighborhoods for even more green space — work up a sweat with a bike ride or jog along The 606, take in lakefront views at the 31st Street Beach, and meander down the boardwalk at Lincoln Park’s South Pond.

Join a tour

A tour is one of the best ways to make the most of your Chicago visit. Learn about the city’s iconic architecture with Free Tours by Foot, Inside Chicago Walking Tours, and Chicago Detourswalking tours. Or see the city on two wheels via a bike or Segway tour with Bike and Roll Chicago or Bobby’s Bike Hike. You can also explore Chicago’s unique neighborhoods with a friendly local for free through Chicago Greeter Tours.

Fall in love with public art

Public art in Chicago is splashed on surfaces all around the city: it covers train stations, rises tall on downtown skyscrapers, and pops up on sidewalks, in office lobbies, and along the lakefront. Discover works of public art in the Loop by masters such as Picasso and Chagall, check out neighborhood street art, or see international street artists make their mark on districts like the Wabash Arts Corridor. Take a public art tour, or create your own. Either way, get your camera ready, and start Instagramming!


Note: Stay tuned for more information about the following events in 2021.

Hear music at a museum

Jazzin at the Shedd

Head to the Shedd Aquarium for Jazzin’ at the Shedd every Wednesday night this August. The evening features live tunes from a top Chicago jazz ensemble, sweeping views of the city skyline, and open access to the Shedd’s many immersive exhibits.

Catch a movie under the stars

The Millennium Park free summer film series is screened under the stars at the iconic Jay Pritzker Pavilion on Tuesdays from June through August. Guests take a seat at the Pavilion or lounge on the Great Lawn with a picnic as both old favorite and new blockbusters are presented on a state-of-the-art, 40-foot LED screen.